By the way, since there are a couple of OpenSSL-related issues floating around right now - could you please help me summarize so that I can get a better overview whether there are open issues that would need to be addressed in Ruby's OpenSSL?

But regarding the problem on OS X, there seemed to be several issues causing similar but unrelated problems. There was one problem related to RubyGems server settings, which has been fixed. Were there also problems related to what nobu fixed with this patch? Are there other open issues on OS X that yet remain to be identified?

The first reactions seemed to imply that upgrading to 1.0.1 would somehow fix the issues, but I doubt it, especially in the case where certificate validation failed.